♾️ The Perfectionist's Nightmare

“John” thought he'd landed his dream client: a well-funded tech startup with an apparently straightforward request for a new logo. Six months later, he found himself trapped in what he now calls "the project that almost ended my design career.”

The trouble began with deceptively simple feedback. "Make it pop more" became the client's mantra, followed by increasingly nebulous requests like "We need something more disruptive" and "It should feel more... you know?" What started as a two-week project morphed into an endless cycle of revisions, with each new iteration disappearing into what John describes as "a black hole of vague critiques and shifting expectations."

The impact on John's business was severe. A project initially quoted at $2,500 had consumed over 200 unbilled hours, forcing him to turn away $15,000 worth of other work. His portfolio, once updated monthly with fresh projects, remained static. "I was tweaking the same logo for so long that potential clients started asking if I was still actively designing," he recalls.

The personal toll proved even steeper. John's typical 40-hour workweek ballooned to 70 hours as he juggled existing clients while desperately trying to satisfy the startup's endless revision requests. His savings dwindled as billable hours evaporated into countless "quick fixes" and emergency client calls. "I went from being excited about work to dreading every email notification," he says. "I was running on energy drinks and stress, watching my creativity drain away with each new round of feedback."

This fictitious case study was developed with the help of Anthropic's Claude models for educational purposes only.